1-O-(2,3-di-O-allyl-4,6-O-benzylidene-β-D-mannopyranosyl)-3-O-tert-butyldimethylsilyl-2,4-O-ethylidene-D-erythritol

Base Information

Chemical Name:1-O-(2,3-di-O-allyl-4,6-O-benzylidene-β-D-mannopyranosyl)-3-O-tert-butyldimethylsilyl-2,4-O-ethylidene-D-erythritol
CAS No.:407616-87-9
Molecular Formula:C₃₁H₄₈O₉Si
Molecular Weight:592.802
Hs Code.:

Synonyms:1-O-(2,3-di-O-allyl-4,6-O-benzylidene-β-D-mannopyranosyl)-3-O-tert-butyldimethylsilyl-2,4-O-ethylidene-D-erythritol

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Chemical Property of 1-O-(2,3-di-O-allyl-4,6-O-benzylidene-β-D-mannopyranosyl)-3-O-tert-butyldimethylsilyl-2,4-O-ethylidene-D-erythritol

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Technology Process of 1-O-(2,3-di-O-allyl-4,6-O-benzylidene-β-D-mannopyranosyl)-3-O-tert-butyldimethylsilyl-2,4-O-ethylidene-D-erythritol

There total 6 articles about 1-O-(2,3-di-O-allyl-4,6-O-benzylidene-β-D-mannopyranosyl)-3-O-tert-butyldimethylsilyl-2,4-O-ethylidene-D-erythritol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

: 407616-81-3
2,4-O-ethylidene-3-O-tert-butyldimethylsilyl-D-erythritol

: 407616-84-6
(R_S)-S-phenyl 2,3-di-O-allyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside S-oxide

: 407616-87-9
1-O-(2,3-di-O-allyl-4,6-O-benzylidene-β-D-mannopyranosyl)-3-O-tert-butyldimethylsilyl-2,4-O-ethylidene-D-erythritol

Guidance literature:: (R_S)-S-phenyl 2,3-di-O-allyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside S-oxide; With trifluoromethylsulfonic anhydride; 3 A molecular sieve; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -75 ℃; for 0.25h;

2,4-O-ethylidene-3-O-tert-butyldimethylsilyl-D-erythritol; In dichloromethane; at -70 ℃; for 1h;
DOI:10.1016/S0040-4020(01)01087-0

Reference yield: 66.0%

: 407616-81-3
2,4-O-ethylidene-3-O-tert-butyldimethylsilyl-D-erythritol

: 407616-82-4
S-phenyl 2,3-di-O-allyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside

: 407616-87-9
1-O-(2,3-di-O-allyl-4,6-O-benzylidene-β-D-mannopyranosyl)-3-O-tert-butyldimethylsilyl-2,4-O-ethylidene-D-erythritol

Guidance literature:: S-phenyl 2,3-di-O-allyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside; With 1-benzenesulfinyl piperidine; 3 A molecular sieve; 2,4,6-tri-tert-butylpyrimidine; trifluoromethylsulfonic anhydride; In dichloromethane; at -60 ℃; for 0.0833333h;

2,4-O-ethylidene-3-O-tert-butyldimethylsilyl-D-erythritol; In dichloromethane; at -60 - 20 ℃;
DOI:10.1016/S0040-4020(01)01087-0

Reference yield:

: 407616-79-9
2,4-O-ethylidene-3-O-tert-butyldimethylsilyl-D-erythrose diethyl thioacetal

: 407616-87-9
1-O-(2,3-di-O-allyl-4,6-O-benzylidene-β-D-mannopyranosyl)-3-O-tert-butyldimethylsilyl-2,4-O-ethylidene-D-erythritol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 86 percent / NBS; water / acetonitrile / 0.5 h / -20 °C

2.1: 80 percent / sodium borohydride / CH₂Cl₂; ethanol / 2 h / 20 °C

3.1: 1-(benzenesulfinyl)piperidine; 2,4,6-tri-tert-butylpyrimidine; 3 Angstroem molecular sieves / triflic anhydride / CH₂Cl₂ / 0.08 h / -60 °C

3.2: 66 percent / CH₂Cl₂ / -60 - 20 °C

With sodium tetrahydroborate; N-Bromosuccinimide; 1-benzenesulfinyl piperidine; 3 A molecular sieve; water; 2,4,6-tri-tert-butylpyrimidine; trifluoromethylsulfonic anhydride; In ethanol; dichloromethane; acetonitrile;
DOI:10.1016/S0040-4020(01)01087-0